Benzimidazolo-diazepines From 1,3-dienes and Arenediazocyanides Through a 1,3,4-tri-aza-cope Rearrangement

Rousselle, D.;Ryckmans, T.;Viehe, HG.
(1992) Tetrahedron — Vol. 48, n° 25, p. 5249-5258 (1992)

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  • Rousselle, D.
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  • Ryckmans, T.
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  • Viehe, HG.
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Abstract
Cyclic and bicyclic 1-cyano-2-arylhydrazines were prepared from arene diazocyanides and 1,3-dienes. Some of them rearrange at room temperature through a 1,3,4-triaza-Cope rearrangement, followed by an intramolecular cyclisation, to afford benzimidazolo-diazepines in moderate yields. When the competitive retro Diels-Alder reaction is made impossible by reduction of the cycloadducts, the rearrangement takes place at higher temperatures, with excellent yields, to previously unknown benzimidazolo-diazepines.
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Rousselle, D., Ryckmans, T., & Viehe, HG. (1992). Benzimidazolo-diazepines From 1,3-dienes and Arenediazocyanides Through a 1,3,4-tri-aza-cope Rearrangement. Tetrahedron, 48(25), 5249-5258. https://doi.org/10.1016/S0040-4020(01)89022-0 (Original work published 1992)